Phthalimide → HCID 68308945, compound

HRID 1021272Notes

Reaction equation

HRID 1021272 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:20]O.[C:22]1(=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[NH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:20][N:23]1[C:24](=[O:31])[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]1=[O:32]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68308912HCID 68308912, compound

Product 1

HCID 68308945HCID 68308945, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-Fluoro-3-[2-(morpholin-4-yl)pyrimidin-5-yl]phenyl}methanol (337 mg), 1H-isoindole-1,3(2H)-dione (257 mg) and triphenylphosphine (458 mg) were mixed with THF, and diethyl azodicarboxylate (40% toluene solution) (0.68 ml) was added thereto at 0° C., followed by stirring at room temperature overnight. The reaction mixture was stirred at 0° C. for 30 minutes, then filtered, washed with ice-cooled THF, and dried at 50° C. under reduced pressure to obtain 2-{2-fluoro-3-[2-(morpholin-4-yl)pyrimidin-5-yl]benzyl}-1H-isoindole-1,3(2H)-dione (452 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  4. filtrationfiltered
  5. washwashed with ice-
  6. temperaturecooled THF
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-bb59ec5946a8424dabdc4f6ea002788e
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

Loading…