Carbon tetrabromide → HCID 11699537, compound

HRID 2353827Notes

Reaction equation

HRID 2353827 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([CH2:31][CH2:32]O)=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:54]>C1COCC1.C(Cl)Cl.CCOC(C)=O>[Br:54][CH2:32][CH2:31][C:29]1[CH:28]=[CH:27][C:26]2[C:19]3[C:18]([NH:17][C:4]4[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=5)=[C:2]([Cl:1])[CH:3]=4)=[N:23][CH:22]=[N:21][C:20]=3[S:24][C:25]=2[CH:30]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11648654HCID 11648654, compound

Product 1

HCID 11699537HCID 11699537, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To a solution of 2-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino) [1]benzothieno[2,3-d]pyrimidin-7-yl]ethanol (700 mg, 1.46 mmol, 1 equiv) in THF (10 mL) were added triphenylphosphine (0.82 g, 3.12 mmol, 3 equiv) and carbon tetrabromide (1.03 g, 3.12 mmol, 3 equiv). The resulting solution was stirred at rt for 14 h and the solvent was evaporated under reduced pressure. The resulting crude material was purified by flash chromatography eluting with 9:1 CH2Cl2/EtOAc yielding a light yellow solid (688 mg, 1.27 mmol, 87%). 1H-NMR (CDCl3) δ 8.60 (s, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.81 (s, 1H), 7.75 (d, J=2.7 Hz, 1H), 7.50-7.44 (m, 3H), 7.39-7.34 (m, 1H), 7.23 (m, 2H), 7.03 (td, 1H), 7.00 (d, J=9.0 Hz, 1H), 5.12 (s, 2H), 3.68 (t, 2H), 3.36 (t, 2H); LCMS RT=4.26 min, [M+H]+=541/544

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe resulting crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-bbc0c20ee99942e2895d809394df4e18
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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