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

HRID 2267550Notes

Reaction equation

HRID 2267550 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][NH:59][CH:60]2[CH2:64][CH2:63][CH2:62][CH2:61]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>[CH:60]1([NH:59][CH2:58][CH2:57][CH2:56][S:53]([N:50]2[CH2:49][CH2:48][CH:47]([C:38]3[C:37]4[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=[C:35]([C:25]5[CH:24]=[CH:23][CH:22]=[C:21]([CH2:31][OH:32])[CH:20]=5)[CH:36]=4)[NH:40][CH:39]=3)[CH2:52][CH2:51]2)(=[O:54])=[O:55])[CH2:64][CH2:63][CH2:62][CH2:61]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 590033255-bromo-3-(1-{[3-(cyclopentylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 590033573-(1-{[3-(cyclopentylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared according to the general procedure for intermediate 16. Thus, 5-bromo-3-(1-{[3-(cyclopentylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (46 mg, 0.09 mmol), [3-(hydroxymethyl)phenyl]boronic acid (55 mg, 0.36 mmol), Pd(PPh3)4 (10 mg, 10%) and cesium carbonate (117 mg, 0.36 mmol) were heated in microwave at 160° C. for 40 min to yield the desired product (16.5 mg, 34%), 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)

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-bf0d75d20ca54fedb6f27db6ea0cb6a8
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

Loading…