Lithium hydroxide, monohydrate → 4-[4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid lithium salt

HRID 1295669Notes

Reaction equation

C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:31][C:14]3[N:15]=[CH:16][N:17]=[C:18]([O:19][C:20]4[C:21]([F:30])=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][C:24]([CH3:29])=[CH:23]5)[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)C.O[Li:34].O>O1CCOCC1.O>[Li+:34].[F:30][C:21]1[C:20]([O:19][C:18]2[C:13]3[CH:12]=[C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:4]([O-:32])=[O:3])=[CH:10][CH:9]=4)[NH:31][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[C:24]([CH3:29])[NH:25]2

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 2.87 g (6.7 mMol) of 4-[4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester and 520 mg (12 mMol) LiOH.H2O in 240 ml of dioxane and 5 ml of water is stirred for 24 h at 120° C. The solid is dissolved first, then a new precipitate is formed. Filtration at RT and washing with dioxane and diethylether gives the title compound; HPLC (conditions see Examples 67-78) tR=13.5 min; MS-ES+: (M+H)+=403.

Workup

dissolutionThe solid is dissolved first
customa new precipitate is formed
filtrationFiltration at RT
washwashing with dioxane and diethylether

Sources & evidence

ORD record: ord-905c3f3da20b406bbbbb77921ae1021c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244729B2

Reaction notes

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