Water → HCID 69084584, compound

HRID 594760Notes

Reaction equation

HRID 594760 reaction equation
N1C=CC([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[S:28][CH:29]=[CH:30][N:31]=4)[CH:22]=3)C(=O)[CH2:17][CH2:16][CH2:15][CH2:14]2)=CC=1.[C:33]1(B(O)O)[CH:38]=CC=[CH:35][CH:34]=1.[C:42]([O-:45])([O-])=O.[Na+].[Na+].O.CCO[C:52]([CH3:54])=O>C1COCC1.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>[C:9]1([C:52]2[CH:54]=[CH:35][CH:34]=[CH:33][CH:38]=2)[CH:10]=[CH:11][CH:12]=[CH:7][C:8]=1[CH:13]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH:22]=2)[C:42](=[O:45])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69084093HCID 69084093, compound

Product 1

HCID 69084584HCID 69084584, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-(2-bromophenyl)-1-(3-(thiazol-2-yl)benzyl)azepan-2-one (preparation described in example 450; 50 mg; 0.11 mmol), commercially available phenylboronic acid (15 mg; 0.12 mmol), and Pd(PPh3)4 (7 mg; 0.006 mmol) in THF (2 ml), and aq. 2 M Na2CO3 (0.2 ml) was heated to 80° C., under nitrogen, for 24 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.98 min.; [M+H]+: 439.16 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

Sources & evidence

ORD record
ord-173e25ff9814405a9c7079b0c0ac3a18
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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