Boron → HCID 67016307, compound

HRID 1919109Notes

Reaction equation

HRID 1919109 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[B].[C:25]([O:28][CH2:29][C:30]1[C:35]([N:36]2[CH2:48][CH2:47][N:39]3[C:40]4[CH2:41][CH2:42][CH2:43][CH2:44][C:45]=4[CH:46]=[C:38]3[C:37]2=[O:49])=[CH:34][CH:33]=[CH:32][C:31]=1Br)(=[O:27])[CH3:26]>CO>[C:25]([O:28][CH2:29][C:30]1[C:31]([C:2]2[CH:3]=[C:4]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)=[CH:13][N:12]=3)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=2)=[CH:32][CH:33]=[CH:34][C:35]=1[N:36]1[CH2:48][CH2:47][N:39]2[C:40]3[CH2:41][CH2:42][CH2:43][CH2:44][C:45]=3[CH:46]=[C:38]2[C:37]1=[O:49])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 5462311BoronHCID 58044104HCID 58044104, compoundHCID 58044170HCID 58044170, compound

Product 1

HCID 67016307HCID 67016307, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following Example 306b, 307a (422 mg, 1.26 mmol) was converted to the boron intermediate 307b, which was coupled under Suzuki conditions with 109a (420 mg, 1.0 mmol). The crude product was purified via column chromatography: ISCO 24 g silica, 50-100% ethyl acetate/hexanes then 0-10% MeOH, to give 307c (285 mg, 36% yield).

Workup

  1. customThe crude product was purified via column chromatography

Sources & evidence

ORD record
ord-5009a4e3c18649fa951137894ef9c3db
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…