Sodium Bicarbonate → HCID 58233790, compound

HRID 1942118Notes

Reaction equation

HRID 1942118 reaction equation
[F:1][C:2]1(F)[CH2:16][CH2:15][C:5]2([O:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH:7]=[CH:6]2)[CH2:4][CH2:3]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH2:16][CH2:15][C:5]2([O:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH:7]=[CH:6]2)[CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58233770HCID 58233770, compound2×

Product 1

HCID 58233790HCID 58233790, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,4-Difluorospiro[cyclohexane-1,2′-pyrano[2,3-b]pyridine] (87) DAST (0.36 ml, 2.7 mmol) was added to a stirred ice-cooled solution of 4H-spiro[cyclohexane-1,2′-pyrano[2,3-b]pyridin]-4-one (85) (0.29 g, 1.3 mmol) in DCM (30 mL) under N2. The resulting mixture was allowed to warm up to rt and stirred at ambient temperature for 21 h. The mixture was poured into ice and saturated NaHCO3 aqueous solution and extracted with DCM (2×). The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a 2; 1 mixture of 4,4-difluorospiro[cyclohexane-1,2′-pyrano[2,3-b]pyridine] (87) and 4-fluorospiro[cyclohex-3-ene-1,2′-pyrano[2,3-b]pyridine] (88) (0.25 g, 80% yield). This material was taken onto the next step without separation. LCMS-ESI (POS), M/Z, M+1: Found 238.1.

Workup

  1. extractionextracted with DCM (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a 2

Sources & evidence

ORD record
ord-4cce48709458416d879517a370e47b74
Source dataset
uspto-grants-2013_03
Patent number
US08389533B2

Reaction notes

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