Carbon tetrabromide → HCID 58346481, compound

HRID 222013Notes

Reaction equation

HRID 222013 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3[C:16]4[CH2:24][CH2:23][C:22]5[C:18](=[CH:19][N:20]([CH2:25][CH2:26]O)[N:21]=5)[C:17]=4[S:28][C:14]=3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>C(Cl)Cl>[Br:49][CH2:26][CH2:25][N:20]1[CH:19]=[C:18]2[C:22]([CH2:23][CH2:24][C:16]3[C:15]4=[C:10]([NH:9][C:4]5[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=5)[N:11]=[CH:12][N:13]=[C:14]4[S:28][C:17]=32)=[N:21]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11524499HCID 11524499, compound

Product 1

HCID 58346481HCID 58346481, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-{6-[(3-chloro-4-fluorophenyl)amino]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl}ethanol (11.4 g, 27.4 mmol) in CH2Cl2 (240 mL) were added triphenylphosphine (13.5 g, 48.0 mmol) and carbon tetrabromide (17.0 g, 48 mmol). The mixture was stirred at room temperature for 1.5 h, and the solvent was then removed under reduced pressure. The crude residue was purified via flash chromatography (1:1 hexanes/EtOAc) to afford the desired product (4.0 g, 30%) as an off-white solid. 1H-NMR (CDCl3) δ 3.05 (t, 2H), 3.27 (t, 2H), 3.66 (s, 2H), 4.40 (t, 2H), 6.93 (s, 1H), 7.05 (t, 1H), 7.34-7.40 (m, 1H), 7.44 (s, 1H), 7.78 (dd, 1H), 8.40 (s, 1H); LCMS RT=3.81 min; [M+H]+=478.2, 480.2.

Workup

  1. customthe solvent was then removed under reduced pressure
  2. customThe crude residue was purified via flash chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ff5b977b8e1c4b88b4671953ec438185
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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