Trifluoroacetic acid → 1-Methylethyl 4-{[(2'-fluoro-6'-methyl-2,3'-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate

HRID 423616Notes

Reaction equation

HRID 423616 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25](C)([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:10][N:9]=2)=[CH:6][CH:5]=[C:4]([CH3:29])[N:3]=1.C(O)(C(F)(F)F)=O.C(N(C(C)C)CC)(C)C.ClC(OC(C)C)=O>C(Cl)Cl>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][CH:25]([CH3:26])[CH3:27])=[O:23])[CH2:20][CH2:21]3)=[CH:10][N:9]=2)=[CH:6][CH:5]=[C:4]([CH3:29])[N:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 666732201,1-Dimethylethyl 4-{[(2'-fluoro-6'-methyl-2,3'-bipyridin-5-yl)oxy]methyl}-1-piperidine carboxylate

Product 1

HCID 591777891-Methylethyl 4-{[(2'-fluoro-6'-methyl-2,3'-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (0.166 g, 96%) was prepared as a white solid from 1,1-dimethylethyl 4-{[(2′-fluoro-6′-methyl-2,3′-bipyridin-5-yl)oxy]methyl}-1-piperidinecarboxylate (0.18 g, 0.45 mmol) and TFA (0.35 mL) in CH2Cl2 (10 mL) then diisopropylethylamine (2.0 mL) and isopropyl chloroformate (1.0M in toluene, 0.54 mL, 0.54 mmol) in a manner similar to Example 74. The crude material was purified by chromatography on a silica gel column eluted with 1:10 acetone/CH2Cl2 to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.45-8.35 (m, 2H), 7.82 (d, 1H, J=8.6 Hz), 7.30-7.25 (m, 1H), 7.20-7.10 (m, 1H), 4.91 (septet, 1H, J=6.3 Hz), 4.22 (bs, 2H), 3.89 (d, 2H, J=6.4 Hz), 2.85-2.70 (m, 2H), 2.53 (s, 3H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 388 (M+H).

Workup

  1. customThe crude material was purified by chromatography on a silica gel column
  2. washeluted with 1:10 acetone/CH2Cl2

Sources & evidence

ORD record
ord-f3b5b2ce064b4bd59133ae70bb008d35
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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