Trifluoroacetic acid → 3-[4-(2,3-Difluoro-phenyl)-isoxazol-5-yl]-5-(4-morpholin-4-yl-cyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 269506Notes

Reaction equation

HRID 269506 reaction equation
[CH2:1]1[O:7][CH2:6][C@@H:4](O)[C@H:2]1O.I([O-])(=O)(=O)=O.[Na+].[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[C:22]1[CH:23]=[N:24][O:25][C:26]=1[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[C:33]([C:36]3[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH:37]=3)[CH:34]=2)[NH:29][CH:28]=1.C([BH3-])#N.[Na+].C(O)(C(F)(F)F)=O>O.CO>[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[C:22]1[CH:23]=[N:24][O:25][C:26]=1[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[C:33]([C:36]3[CH2:41][CH2:40][CH:39]([N:42]4[CH2:2][CH2:1][O:7][CH2:6][CH2:4]4)[CH2:38][CH:37]=3)[CH:34]=2)[NH:29][CH:28]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 6417731,4-AnhydroerythritolHCID 5003444Sodium cyanoborohydrideHCID 23667635Sodium periodateHCID 1354403634-{3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo [2,3-b]pyridin-5-yl}-cyclohex-3-enylamine

Product 1

HCID 1354579013-[4-(2,3-Difluoro-phenyl)-isoxazol-5-yl]-5-(4-morpholin-4-yl-cyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridineYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1,4-anhydroerythritol (208 mg, 2 mmol) in water was treated with sodium periodate (400 mg, 4 mmol)for 12 h, transferred to a solution of 4-{3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo [2,3-b]pyridin-5-yl}-cyclohex-3-enylamine (50 mg, 0.12 mmol) in methanol (5 ml). The resulting solution was treated with sodium cyanoborohydride. After the reaction was completed, TFA was added, and the mixture was concentrated and purified by HPLC to give the morpholine product (20 mg) in 36% yield.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-76c952c4dd2d4d5dbe21b65b0b9a4e06
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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