Potassium Carbonate → HCID 67156075, compound

HRID 2196673Notes

Reaction equation

HRID 2196673 reaction equation
[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14](I)[N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=1)=[O:5].[CH3:38][N:39]1[C:47]2[C:42](=[CH:43][C:44](B(O)O)=[CH:45][CH:46]=2)[CH:41]=[CH:40]1.C([O-])([O-])=O.[K+].[K+].CC#N.O>CCOC(C)=O.O.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>[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:44]3[CH:43]=[C:42]4[C:47](=[CH:46][CH:45]=3)[N:39]([CH3:38])[CH:40]=[CH:41]4)[N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 18373917Acetonitrile--water (1/1)HCID 67155817HCID 67155817, compound

Product 1

HCID 67156075HCID 67156075, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2,6-difluoro-N-(2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (27 mg, 40 mmol, 1.0 eq.), 1-methyl-1H-indol-5-ylboronic acid (1.5 eq.), K2CO3 (20 eq.) and Pd(PPh3)4 (0.05 eq.) were taken up in 4:1 MeCN/water (0.7 mL) and heated to 160° C. for 15 minutes under microwave irradiation. The mixture was diluted with 1:1 EtOAc/water (6 mL), filtered through GF/F paper, and the layers were separated. The organic layer was dried over MgSO4, filtered, and concentrated to afford 2,6-difluoro-N-(2-(1-methyl-1H-indol-5-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (19 mg, 70%).

Workup

  1. filtrationfiltered through GF/F paper
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33c486bca3eb4334a79d8e5cc7823701
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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