Carbon tetrabromide → HCID 58774549, compound

HRID 1292958Notes

Reaction equation

HRID 1292958 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[C:17]4[CH2:18][CH2:19][CH:20]([CH2:22][CH2:23]O)[CH2:21][C:16]=4[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>C1COCC1>[Br:45][CH2:23][CH2:22][CH:20]1[CH2:19][CH2:18][C:17]2[C:10]3[C:9]([NH:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:15][C:16]=2[CH2:21]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17990040HCID 17990040, compound

Product 1

HCID 58774549HCID 58774549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (20 mL) was added 0.63 (102, 1.56 mmol, 1 equiv) of 2-{4-[(3-bromophenyl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-7-yl}ethanol, 0.82 g (3.12 mmol, 2 equiv) triphenylphosphine and 1.03 g (3.12 mmol, 2 equiv) carbon tetrabromide. The solution was stirred at rt for 1 h until completion and the reaction mixture was evaporated under reduced pressure. The resulting crude material was purified by flash chromatography eluting with 9:1 CH2Cl2/EtOAc yielding 396 mg (54%) of a light yellow solid. 1H-NMR (CDCl3-d) δ 8.52 (s, 1H), 7.94 (m, 1H), 7.58 (m, 1H), 7.24 (m, 2H), 7.10 (s, 1H), 3.56 (m, 2H), 3.15 (m, 2H), 3.03 (m, 1H), 2.57 (m, 1H), 2.19 (m, 2H), 2.04 (m, 2H), 1.68 (m, 1H); TLC Rf=0.30 (9:1 CH2Cl2/EtOAc); LCMS RT=3.92 min; [M+H]+=466.2.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customThe resulting crude material was purified by flash chromatography
  3. washeluting with 9:1 CH2Cl2/EtOAc yielding 396 mg (54%) of a light yellow solid

Sources & evidence

ORD record
ord-0889c66d0d3444c8a33d86a22432ce22
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

Loading…