Sodium hydride → HCID 118318852, compound

HRID 921191Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([O:10][CH:11]([CH2:16][CH:17]=[CH2:18])[C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH2:19]([O:22][C:23]1([CH3:52])[CH2:28][CH2:27][N:26]([C:29]2[N:34]3[N:35]=[C:36]([CH2:38]I)[CH:37]=[C:33]3[N:32]=[C:31]([CH3:40])[C:30]=2[C@H:41]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:25][CH2:24]1)[CH:20]=[CH2:21].[H-].[Na+]>CN(C=O)C>[C:48]([O:47][C@@H:41]([C:30]1[C:31]([CH3:40])=[N:32][C:33]2[N:34]([N:35]=[C:36]([CH2:38][O:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[O:10][CH:11]([CH2:16][CH:17]=[CH2:18])[C:12]([F:13])([F:14])[F:15])[CH:37]=2)[C:29]=1[N:26]1[CH2:25][CH2:24][C:23]([CH3:52])([O:22][CH2:19][CH:20]=[CH2:21])[CH2:28][CH2:27]1)[C:42]([O:44][CH2:45][CH3:46])=[O:43])([CH3:51])([CH3:49])[CH3:50]

Participants

Conditions

Temperature: 0 °C

Procedure

(4-Fluoro-2-((1,1,1-trifluoropent-4-en-2-yl)oxy)phenyl)methanol (66 mg, 0.25 mmol) and (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(iodomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (145 mg, 0.25 mmol) were dissolved in 1 mL of DMF at 0° C. and 60% (mineral oil) NaH (10 mg, 0.25 mmol) added. The resulting mixture was stirred at 0° C. for 3 hours then quenched with 1N HCl. The mixture was extracted with ethyl acetate. The organic fractions were combined and dried over Na2SO4, filtered and the solvent removed to yield the crude product which was used in the next reaction without further purification.

Workup

customthen quenched with 1N HCl
extractionThe mixture was extracted with ethyl acetate
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent removed

Sources & evidence

ORD record: ord-50efdcfe63ba4819822e3d0d0b3b5cf5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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