4-Bromo-2-methoxy-1,3-thiazole → HCID 178494028, compound

HRID 252270Notes

Reaction equation

HRID 252270 reaction equation
B(O)O.C([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1)(=[O:11])=[O:10])(C)(C)C.Br[C:20]1[N:21]=[C:22]([O:25][CH3:26])[S:23][CH:24]=1>>[CH3:26][O:25][C:22]1[SH:23]=[CH:24][CH:20]([C:15]2[CH:16]=[CH:17][C:12]([S:9]([NH2:8])(=[O:10])=[O:11])=[CH:13][C:14]=2[CH3:18])[N:21]=1

Participants

3

Reactant 2

HCID 27632664-Bromo-2-methoxy-1,3-thiazoleHCID 178425957HCID 178425957, compound

Product 1

HCID 178494028HCID 178494028, compoundYield 24.6%

Procedure

This compound was prepared analogously to Example 52, starting from N-tert-butyl-3-methyl-benzenesulfonamide boronic acid (1.0 g, 3.69 mmol) and 4-bromo-2-methoxy-thiazole (0.78 g, 4.05 mmol, 1.1 equiv.) After purification on silica-gel with n-heptane/tert.butylmethyl ether 510 mg of the t-butyl protected sulfonamide were obtained. Deprotection analogous to Example 98 yielded 260 mg of the title compound as a light yellow solid. MS (ES): m/e 270 (M−H)

Workup

  1. customThis compound was prepared analogously to Example 52
  2. customAfter purification on silica-gel with n-heptane/tert.butylmethyl ether 510 mg of the t-butyl
  3. customwere obtained

Sources & evidence

ORD record
ord-401be3e2210c4c17a40303b4e7efe321
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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