Benzyl Bromide → HCID 178464431, compound

HRID 340036Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[CH2:24][CH2:23][NH:22][CH2:21][C:20]=5[N:25]=4)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[C:5]([CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:4][C:3]=1[OH:31].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:17]([NH:18][CH2:19][CH3:20])[CH3:12].[CH2:32]([N:22]1[CH2:23][CH2:24][C:19]2[NH:18][C:17]([C:12]3[C:11]4[C:15](=[CH:16][C:8]([C:6]5[C:5]([CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:4][C:3]([OH:31])=[C:2]([F:1])[CH:7]=5)=[CH:9][CH:10]=4)[NH:14][N:13]=3)=[N:25][C:20]=2[CH2:21]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-5-(2,2,2-trifluoro-ethyl)-phenol (Preparation 39, 100 mg, 168 μmol) in DMF (1 mL), was added benzyl bromide (28.8 mg, 20 μL, 168 μmol), and DIPEA (120 μL, 672 μmol). The reaction mixture was heated at 80° C. for 3 hours. The reaction mixture was then cooled to room temperature and saturated aqueous sodium hydrogen carbonate solution (5 mL) was added. The resulting solid was collected by filtration and washed with further saturated aqueous sodium hydrogen carbonate solution. The crude material was purified by HPLC Method A to afford 10.6 mg of the title compound.

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationThe resulting solid was collected by filtration
washwashed with further saturated aqueous sodium hydrogen carbonate solution
customThe crude material was purified by HPLC Method A

Sources & evidence

ORD record: ord-404a6798242e440aba8264bb102e8a26
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895544B2

Reaction notes

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