Sodium Hydroxide → 2',4'-difluoro-5-(6-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-3-yl)biphenyl-3-amine

HRID 64125Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:30]C(=O)C)[CH:10]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[CH:23]=[C:18]3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH2:30])[CH:10]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of the compound of Example 131 (0.5 g, 1.1 mmol) in ethanol (10 ml) was added aqueous solution of NaOH (392 mg, 9.79 mmol, 8.9 eq.) and the mixture was heated at 85° C. for 2 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the product in 79% yield (0.35 g).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off
customto afford the product in 79% yield (0.35 g)

Sources & evidence

ORD record: ord-1ec45ed987c5455789e2b35977f8f27c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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