Ethyl Acetate → HCID 54766120, compound

HRID 920608Notes

Reaction equation

HRID 920608 reaction equation
[F:1][CH:2]([F:30])[O:3][C:4]1[C:9]2[O:10][C:11]3([O:17][C:8]=2[C:7]([C:18](OC2C=CC([N+]([O-])=O)=CC=2)=[O:19])=[CH:6][CH:5]=1)[CH2:16][CH2:15][S:14][CH2:13][CH2:12]3.[Cl:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([Cl:39])[C:37]=1[NH2:38].[H-].[Na+].CCOC(C)=O>C1COCC1.CCCCC>[Cl:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([Cl:39])[C:37]=1[NH:38][C:18]([C:7]1[C:8]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[O:10][C:9]=2[C:4]([O:3][CH:2]([F:30])[F:1])=[CH:5][CH:6]=1)=[O:19]

Participants

7

Reactant 4

HCID 8857Ethyl Acetate2×HCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 67125498HCID 67125498, compound

Product 1

HCID 54766120HCID 54766120, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophenyl 7-difluoromethoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylate (250 mg) and 3,5-Dichloro-4-aminopyridine (129 mg) was dissolved under argon in dry THF, 5 mL. Sodium hydride (50% suspension in oil), 40 mg, was added, and the mixture left stirring overnight. Aqueous work up with EtOAc and chromatography in a gradient from 0 to 60% EtOAc in pentane afforded the title compound. 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 8.57 (s, 2H), 7.63 (d, J=9.0 Hz, 1H), 6.86 (d, J=9.1 Hz, 1H), 6.73 (t, J=72 Hz, 1H), 3.03-2.81 (m, 4H), 2.49-2.29 (m, 4H).

Workup

  1. waitthe mixture left

Sources & evidence

ORD record
ord-85fb439597b248088339c412ad0b1f0c
Source dataset
uspto-grants-2016_03
Patent number
US09273064B2

Reaction notes

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