Acetic Acid → N-(5-bromothiazol-2-yl)-cyclopropylmethylamine

HRID 1670536Notes

Reaction equation

HRID 1670536 reaction equation
C(O)(=O)C.[Br:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1>C(Cl)Cl>[Br:5][C:6]1[S:10][C:9]([NH:11][CH2:29][CH:26]2[CH2:28][CH2:27]2)=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 436002-Thiazolamine, 5-bromo-HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59822318N-(5-bromothiazol-2-yl)-cyclopropylmethylamineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic acid (2 mL, 33.4 mmol) to a mixture of 5-bromo-thiazol-2-ylamine (1 g, 5.6 mmol), sodium triacetoxyborohydride (3.5 g, 16.7 mmol) and cyclopropane carboxaldehyde (820 mg, 11.7 mmol) at room temperature under a nitrogen atmosphere. Stir the resulting solution for 1.5 h at ambient temperature. Dilute the solution with DCM (50 mL) and wash with saturated aqueous NaHCO3 (80 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (9:1 to 7:3 gradient) to obtain the title compound (970 mg, 75%). MS (ES+) m/z: 233.1 (M+).

Workup

  1. washwash with saturated aqueous NaHCO3 (80 mL)
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by chromatography on silica gel (40 g)
  6. washeluting with hexane/EtOAc (9:1 to 7:3 gradient)

Sources & evidence

ORD record
ord-f3187df32cfd4517987610280afe49d7
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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