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Sodium Bicarbonate → 2-[(4-(5-Fluoro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline

HRID 431013
Notes
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Reaction equation

HRID 431013 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][C@@H:2]1[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)[N:11]=[CH:10][N:9]=[CH:8]3.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH:42]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C:37]1[CH2:38][CH2:39][N:40]([CH2:15][CH:2]2[O:1][C:6]3=[C:7]4[C:12](=[CH:13][CH:14]=[C:5]3[O:4][CH2:3]2)[N:11]=[CH:10][N:9]=[CH:8]4)[CH2:41][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 12095706(2R)-2,3-Dihydro-1,4-dioxino[2,3-f]quinazolin-2-ylmethyl-4-methylbenzenesulfonate

Product 1

HCID 101125952-[(4-(5-Fluoro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline

Reagents, catalysts & solvents 1

HCID 21974620
tetrahydrofuran N,N-dimethylformamide
Solvent

Procedure

(2R)-2,3-Dihydro-1,4-dioxino[2,3-f]quinazolin-2-ylmethyl-4-methylbenzenesulfonate (800 mg, 3.7 mmole) was dissolved in a mixture of DMF/THF 1:1 v/v (30 mL) and 5-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (800 mg, 4 mmole) added, followed by the addition of sodium bicarbonate (1.0 gm, 9.4 mmole) and the mixture was refluxed under nitrogen for 18 hours. The solvent was evaporated under vacuum and the residue partitioned between methylene chloride and water. The organic phase was separated, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to a foam. Treatment of this foam with 3% methanol in chloroform yielded 320 mg (35%) of the (S)-enantiomer of the title compound as a yellow crystalline hemihydrate, m.p. 233-235° C.

Workup

  1. additionadded
  2. temperaturethe mixture was refluxed under nitrogen for 18 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue partitioned between methylene chloride and water
  5. customThe organic phase was separated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to a foam

Sources & evidence

ORD record
ord-217642dea49645f69afa9fd4fb7d5af4
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06656947B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes