Sodium Carbonate → 5-(3'-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile

HRID 506151Notes

Reaction equation

HRID 506151 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([C:15]=2[NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)[C:13]#[N:14])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[NH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1>COCCOC.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>[NH2:32][C:33]1[CH:34]=[C:35]([C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([C:8]3[CH:9]=[N:10][CH:11]=[C:12]([C:15]=3[NH:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[C:13]#[N:14])[CH:5]=2)[CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 248666815-(3-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile

Product 1

HCID 248668485-(3'-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-(3-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile 113 (39 mg, 0.1 mmol), (Ph3P)4Pd (2.3 mg, 0.002 mmol) and 2M aq. Na2CO3 (0.1 mL) in DME (2 mL) was degassed by bubbling nitrogen for 5 min., then 3-aminophenylboronic acid (17 mg, 0.11 mmol) was added and the mixture was heated at reflux for 12 h. After cooling to r.t., the mixture was filtered and the filtrate was purified by preparative HPLC to give 5-(3′-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile 117. MS: 402 (M+H), HPLC retention time: 1.72 min.(a).

Workup

  1. customwas degassed
  2. customby bubbling nitrogen for 5 min.
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 12 h
  5. filtrationthe mixture was filtered
  6. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-a34c42b4b08c4635a38dd8fb77a27657
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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