Water → HCID 86704018, compound

HRID 1773928Notes

Reaction equation

HRID 1773928 reaction equation
I[C:2]1[N:11]2[C:5]([CH:6]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10]2)=[N:4][C:3]=1I.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:23][N:20]1[CH2:21][CH2:22][CH:17]([O:16][CH:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][N:11]3[C:5]2=[N:4][C:3]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:8]=2)=[C:2]3[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 962WaterHCID 66827Phenylboronic AcidHCID 86703994HCID 86703994, compound

Product 1

HCID 86704018HCID 86704018, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 1,2-diiodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 219A) (212 mg, 0.386 mmole) in THF (3 mL) are added benzeneboronic acid (120 mg, 1 mmole), water (3 mL), Ba(OH)2 (460 mg, 2 mmoles) and PdCl2(dppf)2 (40 mg). The flask is evacuated and filled with argon. The reaction mixture is heated at 105° C. for 48 hours. AcOEt is added and the organic phase is washed with water, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) (100:0) to (95:5) to give 4-(1-methylpiperidin-4-yloxy)-1,2-diphenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene melting at 90° C.

Workup

  1. customThe flask is evacuated
  2. additionfilled with argon
  3. additionAcOEt is added
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with (CH2Cl2:MeOH) (100:0) to (95:5)

Sources & evidence

ORD record
ord-d5e382b4b59e4618a2170ec313056cbc
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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