Acetic Acid → HCID 68935090, compound

HRID 2218727Notes

Reaction equation

HRID 2218727 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:18]=3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:32]=1.CC(O)=[O:35].O.OO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[CH:16][C:17]3[CH:18]=[C:19]([OH:35])[CH:20]=[CH:21][CH:22]=3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 68937349HCID 68937349, compound

Product 1

HCID 68935090HCID 68935090, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 8-chloro-11-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (300 mg, 0.68 mmol), HOAc (1 mL), water (1 mL), THF (5 mL) and 30% H2O2 (mL). Stir the reaction at RT for 4 h. Quench with aqueous Na2S2O3 and extract the product into EtOAc. Dry (MgSO4) and concentrate to give 250 mg crude product. Purify by column chromatography (15% ethyl acetate/hexane) to give 66 mg 3-(8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidenemethyl)-phenol, Z-isomer as a white solid, mp 221.2° C. MS (ES) 334 (M+1), 332 (M−1). HPLC shows 99% purity.

Workup

  1. customthe reaction at RT for 4 h
  2. customQuench with aqueous Na2S2O3
  3. extractionextract the product into EtOAc
  4. dry with materialDry (MgSO4)
  5. concentrationconcentrate
  6. customto give 250 mg crude product
  7. customPurify by column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b91ce689e44a4aa583a2a05e2b1736ce
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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