Trifluoroacetic acid → 3-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 418666Notes

Reaction equation

HRID 418666 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:32]C(=O)OC(C)(C)C)[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23]([C:25]3[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH:30]=3)[S:24][C:17]=12>>[F:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23]([C:25]3[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH:30]=3)[S:24][C:17]=12)[NH2:32]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66649226Tert-butyl 3-fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamate

Product 1

HCID 167179683-Fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 48%

Procedure

TFA (1 mL) was added to tert-butyl 3-fluoro-4-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamate (229) (105 mg, 0.23 mmol) and the mixture was stirred for 1 h at room temperature. The solution was concentrated under reduced pressure, the residue co-distilled with MeCN, redissolved in MeOH and purified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min) giving 230 (50 mg, 0.1 mmol, 48% yield) as a white solid. MS (m/z): (M+1) 356.1 (100%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue co-distilled with MeCN, redissolved in MeOH
  3. custompurified by preparative HPLC (gradient 40% to 95% MeOH in water, 45 min)

Sources & evidence

ORD record
ord-db11334f983e42d69fd56e6da1bae27e
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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