Methanol → HCID 117953296, compound

HRID 1057065Notes

Reaction equation

HRID 1057065 reaction equation
[F:1][C:2]1([F:30])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)[CH:10]=[C:9]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:8]=2)[CH2:3]1.CO.[CH2:33]([Br:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[Br-:40].[CH2:33]([N+:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:9]2[CH:10]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=[CH:16][N:15]=3)[N:12]=[C:7]([N:4]3[CH2:5][CH2:6][C:2]([F:1])([F:30])[CH2:3]3)[CH:8]=2)[CH:25]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7498Benzyl BromideHCID 90067636HCID 90067636, compound

Product 1

HCID 117953296HCID 117953296, compound

Procedure

To a suspension of 6-(3,3-difluoropyrrolidin-1-yl)-4-(3-pyridyl)-N-[4-(trifluoromethyl)-2-pyridyl]pyridin-2-amine (2-c, 320 mg, 0.7594 mmol) in methanol (5 ml, 100 mmol) was added benzyl bromide (0.46 ml, 5.0 equiv., 3.797 mmol), and the reaction was kept at 60° C. overnight. MeOH was removed as much as possible. Ethyl ether (3×10 mL) was used to wash away the excess BnBr. The leftover solid was used without further treatment. LCMS: m/z 512 (M+).

Workup

  1. customMeOH was removed as much as possible
  2. washto wash away the excess BnBr

Sources & evidence

ORD record
ord-688884392ff844a4b280b5f2f06c9076
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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