Carbon tetrabromide → HCID 58529780, compound

HRID 1972934Notes

Reaction equation

HRID 1972934 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:20]=[CH:21][C:22]4[C:26]([CH:27]=3)=[N:25][N:24]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=4)[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:17]O)[CH:14]=[CH:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:55]>O1CCCC1>[CH2:28]([N:24]1[CH:23]=[C:22]2[C:26]([CH:27]=[C:19]([C:8]3[CH:9]=[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][Br:55])[CH:12]=4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:20]=[CH:21]2)=[N:25]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58529400HCID 58529400, compound

Product 1

HCID 58529780HCID 58529780, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]phenyl}methanol (575 mg, 1.29 mmol) and triphenylphosphine (507 mg, 1.93 mmol) in tetrahydrofuran (10 mL) was added carbon tetrabromide (512 mg, 1.55 mmol). The reaction was stirred at rt for 17 h. The mixture was partitioned between water (50 mL) and CH2Cl2 (50 mL). The layers were separated and the organic phase was washed with brine, dried (Na2SO4), and evaporated. The crude material was purified via ISCO® chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 592 mg (90%) of the desired product, which contained a minor impurity. ES-MS m/z 509.41 [M+H]+, HPLC RT (min) 3.31 min.

Workup

  1. customThe mixture was partitioned between water (50 mL) and CH2Cl2 (50 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude material was purified via ISCO® chromatography

Sources & evidence

ORD record
ord-238241fa6631478fa695544709a1545a
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…