Cesium carbonate → 5-[3-(hydroxymethyl)phenyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267545Notes

Reaction equation

HRID 2267545 reaction equation
N1(CCS(N2CCC(C3[C:25]4[C:20](=[C:21]([C:31](N)=[O:32])[CH:22]=[C:23](C5C=CSC=5)[CH:24]=4)NC=3)CC2)(=O)=O)CCCC1.Br[C:35]1[CH:36]=[C:37]2[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=1)[NH:40][CH:39]=[C:38]2[CH:47]1[CH2:52][CH2:51][N:50]([S:53]([CH2:56][CH2:57][CH2:58][N:59]2[CH2:63][CH2:62][CH2:61][CH2:60]2)(=[O:55])=[O:54])[CH2:49][CH2:48]1.OCC1C=C(B(O)O)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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>[OH:32][CH2:31][C:21]1[CH:20]=[C:25]([C:35]2[CH:36]=[C:37]3[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=2)[NH:40][CH:39]=[C:38]3[CH:47]2[CH2:52][CH2:51][N:50]([S:53]([CH2:56][CH2:57][CH2:58][N:59]3[CH2:63][CH2:62][CH2:61][CH2:60]3)(=[O:55])=[O:54])[CH2:49][CH2:48]2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 116200533-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideHCID 590033005-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 116133675-[3-(hydroxymethyl)phenyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared following the general procedure for intermediate 16. Thus, 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (150 mg, 0.30 mmol), [3-(hydroxymethyl)phenyl]boronic acid (188 mg, 1.20 mmol), Pd(PPh3)4 (30 mg, 10%) and cesium carbonate (200 mg, 0.60 mmol) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to yield the desired product (280 mg, 44%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7164a11be59b45069eb2d18b0b64fa53
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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