Ammonia → 1-(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanamine

HRID 2172534Notes

Reaction equation

HRID 2172534 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]([F:37])([F:36])[C:8]1[CH:13]=[C:12]([C:14]2([C:28]([F:31])([F:30])[F:29])[CH2:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25]O)=[C:21]([Br:27])[CH:20]=3)=[N:16][CH2:15]2)[CH:11]=[C:10]([C:32]([F:35])([F:34])[F:33])[N:9]=1.C([N:40](CC)CC)C.N>C1COCC1.CO>[F:6][C:7]([F:37])([F:36])[C:8]1[CH:13]=[C:12]([C:14]2([C:28]([F:31])([F:30])[F:29])[CH2:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH2:40])=[C:21]([Br:27])[CH:20]=3)=[N:16][CH2:15]2)[CH:11]=[C:10]([C:32]([F:35])([F:34])[F:33])[N:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86664623(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol

Product 1

HCID 866646241-(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanamineYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methanesulfonyl chloride (0.17 g) was added to (4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol (0.46 g) and triethylamine (0.26 g) in THF at −10° C. and the resultant mixture was stirred for 30 min. The mixture was poured into ammonia (10 ml), THF (10 ml) and MeOH (10 ml), and the resultant was stirred at room temperature overnight. After the solvents were evaporated under reduced pressure, the residue was diluted with t-BuOMe and H2O, and the organic layer was dried over MgSO4. After the solvents were evaporated under reduced pressure, the residue was purified with column chromatography to get the targeted product (0.4 g).

Workup

  1. customAfter the solvents were evaporated under reduced pressure
  2. additionthe residue was diluted with t-BuOMe and H2O
  3. dry with materialthe organic layer was dried over MgSO4
  4. customAfter the solvents were evaporated under reduced pressure
  5. customthe residue was purified with column chromatography

Sources & evidence

ORD record
ord-8574e523e31747c5810747865c8846af
Source dataset
uspto-grants-2015_06
Patent number
US09055749B2

Reaction notes

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