Selectfluor → (R)-tert-Butyl 1-(7-fluoro-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-3-methoxypropan-2-ylcarbamate

HRID 516083Notes

Reaction equation

[CH3:1][O:2][CH2:3][C@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:5][NH:6][C:7]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[C:10]2[C:21](=[O:24])[NH:22][CH2:23][C:9]=2[CH:8]=1.[B-](F)(F)(F)[F:34].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(Cl)Cl.CCOC(C)=O.C1COCC1.CCOC(C)=O>[F:34][C:8]1[C:9]2[CH2:23][NH:22][C:21](=[O:24])[C:10]=2[C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[N:12][C:7]=1[NH:6][CH2:5][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:3][O:2][CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a screw-top vial was added (R)-tert-butyl 1-methoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate (27 mg, 0.061 mmol) in a mixture of DCM and MeOH (1/1, 1.2 mL). The resulting colorless solution was cooled to 0° C. SELECTFLUOR® (21.66 mg, 0.061 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. Next, the reaction mixture was diluted with EtOAc (10 mL) and washed with saturated aq sodium bicarbonate (5 mL), water (5 mL), and brine (5 mL). The organic layer was collected, dried over Na2SO4, and concentrated to give the title compound as a brown residue, which was used without further purification (32 mg, 114%). [M+H] calc'd for C23H30FN5O4, 460; found, 460.

Workup

washwashed with saturated aq sodium bicarbonate (5 mL), water (5 mL), and brine (5 mL)
customThe organic layer was collected
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-66b2df96e4b1453b8f9e6f56fcbacc07
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108970B2

Reaction notes

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