Cesium carbonate → HCID 10228548, compound

HRID 489118Notes

Reaction equation

HRID 489118 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH2:15][CH2:16][CH2:17][C:12]2=[C:11]2[C:7]=1[C:8]([C:27](=[O:31])[C:28]([NH2:30])=[O:29])=[C:9]([CH3:26])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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>[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH2:15][CH2:16][CH2:17][C:12]2=[C:11]2[C:7]=1[C:8]([C:27](=[O:31])[C:28]([NH2:30])=[O:29])=[C:9]([CH3:26])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 101177372-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(2-bromobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester

Product 1

HCID 10228548HCID 10228548, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(2-bromobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (200 mg, 0.400 mmol), phenylboronic acid (49 mg, 0.40 mmol), cesium carbonate (260 mg, 0.800 mmol), and tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.0012 mmol) in dioxane (20 mL) was sparged with nitrogen for 5 min then heated at 100° C. for 6 h. The mixture was allowed to cool to room temperature and filtered through a pad of silica gel that was subsequently washed with acetone. The filtrate was concentrated in vacuo. Reverse-phase chromatography (C18, water/acetonitrile) of the residue provided 61 mg (31%) of the title compound. 1H NMR (CDCl3) δ 7.49 (t, J=7.0 Hz, 2H), 7.42 (t, J=7.3 Hz, 1H), 7.37 (d, J=7.0 Hz, 2H), 7.29 (m, 2H), 7.17 (m, 1H), 6.56 (bs, 1H), 6.48 (d, J=8.0 Hz, 1H), 6.44 (s, 1H), 5.42 (bs, 1H), 5.26 (s, 2H), 4.68 (s, 2H), 3.76 (s, 3H), 2.86 (t, J=7.3 Hz, 4H), 2.34 (s, 3H), 2.01 (quintet, J=7.0 Hz, 2H); MS FD+ m/e 496 (p); IR (KBr, cm−1) 3461, 1757, 1699, 1642.

Workup

  1. customwas sparged with nitrogen for 5 min
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a pad of silica gel that
  4. washwas subsequently washed with acetone
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-39febbabbeb14659a04b5a946114cdf6
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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