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Water → Benzyl 4-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxy phenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoate

HRID 1952494
Notes
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Reaction equation

HRID 1952494 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[C:14]([C:33]4[CH:48]=[CH:47][C:36]([C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])=[CH:35][CH:34]=4)[N:15]3[CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]3=[O:32])=[CH:11][CH:10]=2)=[O:8])=[CH:4][C:3]=1[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].[F-].[Cs+].[OH:57][C:58]1[CH:59]=[C:60](B(O)O)[CH:61]=[CH:62][CH:63]=1.O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:31]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:32])[N:22]1[CH2:21][CH2:20][CH2:19][CH2:18][N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([C:7]([C:5]3[S:6][C:2]([C:62]4[CH:61]=[CH:60][CH:59]=[C:58]([OH:57])[CH:63]=4)=[C:3]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH:4]=3)=[O:8])[CH:17]=2)[CH:13]=[C:14]1[C:33]1[CH:48]=[CH:47][C:36]([C:37]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[O:38])=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 67495957Benzyl 4-(6-(5-bromo-4-(2-ethoxy-2-oxoethyl)thiophene-2-carbonyl)-1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-indol-2-yl)benzoate

Product 1

HCID 67497144
Benzyl 4-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxy phenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoate
Yield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5 (60 mg, 0.075 mmol), Pd(PPh3)4 (17 mg, 0.015 mmol), CsF (34 mg, 0.22 mmol), 3-hydroxyphenylboronic acid (16 mg, 0.12 mmol), and H2O (80 μL) in DME (8 mL) was degassed with N2 for 10 min and then refluxed. When the reaction was over by TLC monitoring, the mixture was poured into H2O (10 mL) and then extracted with 70 mL Et2O. The organic layer was washed with brine (2×10 mL), dried over MgSO4, and then concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 6 as a yellow amorphous solid (50 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 8.13 (d, J=8.0 Hz, 2H), 8.04 (s, 1H), 7.74-7.61 (m, 7H), 7.56 (d, J=8.0 Hz, 2H), 7.49-7.26 (m, 6H), 7.13 (s, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 6.63 (s, 1H), 5.40 (s, 2H), 4.32 (t, J=7.2 Hz, 2H), 4.16-4.06 (m, 2H), 3.72 (s, 2H), 3.51 (t, J=6.8 Hz, 2H), 1.72-1.69 (m, 2H), 1.49-1.46 (m, 2H), and 1.26 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 188.62, 171.45, 168.65, 166.21, 157.16, 149.47, 143.69, 141.59, 138.00, 137.26, 137.23, 136.09, 134.28, 131.99, 131.82, 130.66, 130.37, 130.33, 130.12, 129.33, 128.90, 128.62, 128.53, 123.49, 121.88, 121.13, 120.87, 116.54, 116.46, 112.82, 104.20, 67.20, 61.46, 43.92, 37.36, 34.81, 27.45, 25.84, and 14.42.

Workup

  1. customwas degassed with N2 for 10 min
  2. temperaturerefluxed
  3. additionthe mixture was poured into H2O (10 mL)
  4. extractionextracted with 70 mL Et2O
  5. washThe organic layer was washed with brine (2×10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customMPLC purification (Hex:EtOAc/5:1) of the residue

Sources & evidence

ORD record
ord-5d27584b83b84762bb217280e136514c
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404728B2

Reaction notes

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