Bromine → HCID 25070531, compound

HRID 559060Notes

Reaction equation

HRID 559060 reaction equation
[Br:1]Br.[CH:3]1([N:6]2[C:15]3[C:10](=[C:11]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=4[F:26])[C:12]([F:17])=[CH:13][C:14]=3[F:16])[C:9](=[O:27])[CH:8]=[CH:7]2)[CH2:5][CH2:4]1>C(O)(=O)C>[Br:1][C:8]1[C:9](=[O:27])[C:10]2[C:15](=[C:14]([F:16])[CH:13]=[C:12]([F:17])[C:11]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=2[F:26])[N:6]([CH:3]2[CH2:5][CH2:4]2)[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 25070530HCID 25070530, compound

Product 1

HCID 25070531HCID 25070531, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (8.4 mg, 0.052 mmol) in acetic acid (0.1 mL) was slowly added to a stirred solution of example 2 (14.4 mg, 0.0316 mmol) in acetic acid (0.4 mL). The reaction mixture was stirred for 3 h. Purification by preparative HPLC mass triggered gave 3 mg (18%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 11.12 (s, 1H), 8.53 (d, 1H, J=1.2 Hz), 7.93 (t, 1H, J=10.4 Hz), 7.63 (d, 1H, J=10.4 Hz), 7.41 (d, 1H, J=8.8 Hz), 6.64-6.71 (m, 1H), 3.94-4.04 (m, 1H), 1.06-1.17 (m, 4H). MS (ES) [m+H] calc'd for C18H11BrF3IN2O, 535; found 535.

Workup

  1. customPurification by preparative HPLC mass

Sources & evidence

ORD record
ord-8a5abedb54c049d5a2d436964db2c861
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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