Bromine → Tert-butyl 4-(4-amino-7-bromothieno[3,2-c]pyridin-3-yl)phenylcarbamate

HRID 17129Notes

Reaction equation

HRID 17129 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][CH:14]=3)=[CH:11][S:12][C:8]=2[CH:7]=[CH:6][N:5]=1>ClCCl>[NH2:3][C:4]1[C:9]2[C:10]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:17][CH:18]=3)=[CH:11][S:12][C:8]=2[C:7]([Br:1])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 18451468Tert-butyl 4-(4-aminothieno[3,2-c]pyridin-3-yl)phenylcarbamate

Product 1

HCID 18451459Tert-butyl 4-(4-amino-7-bromothieno[3,2-c]pyridin-3-yl)phenylcarbamateYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.4 mL, 4.6 mmol) in dichloromethane (5 mL) was added dropwise to a −5° C. solution of Example 76A (1.57 g, 4.6 mmol) in dichloromethane (30 mL). The mixture was stirred at −5° C. to 0° C. for 15 minutes and quenched with 1:1 saturated NaHCO3 and saturated NaHSO3 (10 mL). The organic phase was separated, washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide 1.85 g of the desired product. MS (ESI(+)) m/e 421 (M+H)+.

Workup

  1. customquenched with 1:1 saturated NaHCO3 and saturated NaHSO3 (10 mL)
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb7c52c696649f7b2d2eb2d5b31bf42
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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