Bromine → HCID 10250559, compound

HRID 227501Notes

Reaction equation

HRID 227501 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([NH2:13])=[O:12])=[C:7]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[Br:23]Br>C(O)(=O)C>[NH2:1][C:2]1[C:3]([Br:23])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([NH2:13])=[O:12])=[C:7]2[S:14]([N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 100191367-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

Product 1

HCID 10250559HCID 10250559, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 7-amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide from Example 7 (109 mg, 0.336 mmol) in 5 mL of acetic acid was added a 3.3 M stock solution of bromine in acetic acid (0.12 mL, 0.40 mmol). After 30 minutes, the mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by preparative reversed phase HPLC provided the titled compound. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C13H16BrN4O4S (M+H+): 403.0070. Found 403.0069.

Workup

  1. customthe mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-92f5a14846fd4fe2abafae0d3812158d
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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