Phosphorus tribromide → HCID 58335589, compound

HRID 1890697Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:22]4[N:27]=[C:26](O)[CH:25]=[CH:24][CH:23]=4)=[CH:20][N:21]=3)[N:18]=2)[CH:5]=[CH:6][CH:7]=1.P(Br)(Br)[Br:30]>>[Br:30][C:26]1[N:27]=[C:22]([C:19]2[N:17]3[N:18]=[C:13]([N:9]4[CH2:10][CH2:11][CH2:12][C@@H:8]4[C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH:14]=[CH:15][C:16]3=[N:21][CH:20]=2)[CH:23]=[CH:24][CH:25]=1

Participants

Reactant 2

HCID 24614Phosphorus tribromide

HCID 178515976HCID 178515976, compound

Product 1

HCID 58335589HCID 58335589, compound

Conditions

Temperature: 175 °C

Procedure

In step 16-2, a suspension of crude (R)-6-(6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-ol (16-1) (13.3 g, 35.4 mmol) in PBr3 (25 mL) was heated to 175° C. for 35 minutes. While the mixture was hot, it was poured into ice-cold 2N NaOH (1.2 L). The solid was collected by filtration and washed with H2O. The final product was dried under high vacuum overnight to give (R)-3-(6-bromopyridin-2-yl)-6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine (16-2) as a light-yellow solid which was used in the next step without further purification. LC/MS: 438.2 (M+H+).

Workup

filtrationThe solid was collected by filtration
washwashed with H2O
dry with materialThe final product was dried under high vacuum overnight

Sources & evidence

ORD record: ord-9a5f0dc3422544b7b433ce0301b9c119
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507488B2

Reaction notes

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