tert-Butanol → HCID 66847104, compound

HRID 1466679Notes

Reaction equation

HRID 1466679 reaction equation
[Br:1][C:2]1[S:3][C:4](C(O)=O)=[C:5]([C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][CH3:15])[N:6]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[Br:1][C:2]1[S:3][C:4]([NH:38][C:41](=[O:26])[O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[C:5]([C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[O:14][CH3:15])[N:6]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66847284HCID 66847284, compound

Product 1

HCID 66847104HCID 66847104, compoundYield 66%

Procedure

2-bromo-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylic acid (1.22 g, 3.50 mmol), diphenylphosphoryl azide (963 mg, 3.50 mmol) and triethylamine (354 mg, 3.50 mmol) in tert-butanol (30 mL) were stirred at 85° C. for 4 hours. After cooling, the reaction was partitioned between ethyl acetate and water, the organics separated then washed with brine, and evaporated to dryness. The resulting residues were purified by flash chromatography on silica gel (50 to 100% dichloromethane in cyclohexane) to yield 970 mg (66%) of tert-butyl 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazol-5-ylcarbamate. LCMS (ESI) m+H=421.2; 1H NMR (400 MHz, DMSO-d6): δ 7.43 (dd, 1H), 7.30 (d, 1H); 7.11 (d, 1H); 3.77 (s, 3H); 1.45 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between ethyl acetate and water
  3. customthe organics separated
  4. washthen washed with brine
  5. customevaporated to dryness
  6. customThe resulting residues were purified by flash chromatography on silica gel (50 to 100% dichloromethane in cyclohexane)

Sources & evidence

ORD record
ord-483f7cdaa5dc4e91965b1d9aae5f787d
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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