Carbon tetrabromide → HCID 21959468, compound

HRID 2109643Notes

Reaction equation

HRID 2109643 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[NH:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[N:25][NH:26]3)=[CH:22][CH:21]=2)=[CH:7][C:6]=1[NH:30][CH2:31][CH2:32]O)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:35].C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:35][CH2:32][CH2:31][NH:30][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[NH:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[N:25][NH:26]3)=[CH:22][CH:21]=2)[CH:9]=[CH:10][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 21959398HCID 21959398, compound

Product 1

HCID 21959468HCID 21959468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from N-[4-tert-butyl-3-(2-hydroxy-ethylamino)-phenyl]-2-(1H-indazol-6-ylamino)-nicotinamide by dissolving in CH2Cl2 (5 ml) and adding CBr4 (215 mg) and bis(diphenylphosphino)-propane (270 mg). The reaction was stirred at RT for 3 h then worked up with partitioning between H2O and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×) and the combined organic fractions were washed with H2O, brine and dried (MgSO4). The crude material was purified by flash chromatography to yield a yellow foamed solid. M+H 508.

Workup

  1. customwith partitioning between H2O and CH2Cl2
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. washthe combined organic fractions were washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. customThe crude material was purified by flash chromatography
  6. customto yield a yellow foamed solid

Sources & evidence

ORD record
ord-03c8c7d215064969bfa01aff34bbe5d3
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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