Water → (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate

HRID 1177534Notes

Reaction equation

HRID 1177534 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH:27]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.O>[Pd].C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:19][CH2:18]1)[N:11]=2

Participants

5

Reactant 2

HCID 962WaterHCID 67112968(2S)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2H-pyrrole-1,2(5H)-dicarboxylate

Product 1

HCID 67111920(2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(2S)-1-tert-Butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2H-pyrrole-1,2(5H)-dicarboxylate (0.618 g, 1.1 mmol) and 10% palladium on carbon, 50% water (0.58 g) were combined in a flask and treated with nitrogen and 10 mL THF. The reaction mixture was stirred rapidly under H2 balloon for 48 h. The reaction mixture was flushed with nitrogen, filtered, rinsing with DCM and concentrated in vacuo. Purification by silica gel chromatography, 40 g, 0-30% EA/hexanes gave (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate as a yellow foam. MS (ESI) m/z: Calculated: 573.2; Observed: 573.7 (M++1).

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered
  3. washrinsing with DCM
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography, 40 g, 0-30% EA/hexanes

Sources & evidence

ORD record
ord-6c31b1fdec9540ccaa6e10fd31f10d93
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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