Dichloromethane → HCID 11382501, compound

HRID 268654Notes

Reaction equation

HRID 268654 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][CH3:12])[CH:10]=1)[NH:7][C:6]1[C:13]([CH2:19][CH2:20][OH:21])([CH2:17][CH3:18])[O:14][CH2:15][CH2:16][C:5]2=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ClCCl>COCCOC.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]>[CH2:17]([C:13]1([CH2:19][CH2:20][OH:21])[C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH2:16][CH2:15][O:14]1)=[CH:3][C:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:10][C:9]=3[CH2:11][CH3:12])[CH3:18]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 113370992-(6-Bromo-1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)ethanol

Product 1

HCID 11382501HCID 11382501, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(6-bromo-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanol (3.8 g, 10.8 mmol) in ethylene glycol dimethyl ether (50 mL) was added potassium phosphate (6.37 g, 30 mmol), phenylboronic acid (1.83 g, 15 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane. The reaction mixture was heated at 90° C. (oil bath) overnight. It was quenched with water and extracted with ethyl acetate. Extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 50% ethyl acetate/hexane, followed by Sephadex LH-20, 50% chloroform/hexane) to give the title compound (0.75 g, 20% yield). 1H NMR (CDCl3) δ 7.77 (s, 1H), 7.66 (d, 1H), 7.63 (m, 1H), 7.56 (d, 1H), 7.44 (m, 3H), 7.32 (m, 1H), 4.06 (m, 2H), 3.72 (m, 3H), 2.91 (m, 3H), 2.81 (dt, 1H), 2.65 (dd, 1H), 2.20 (m, 1H), 2.07 (m, 2H), 1.40 (t, 3H), 0.95 (t, 3H). ES-MS (m/z) 348 [M−1]−.

Workup

  1. customIt was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialExtracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel, 50% ethyl acetate/hexane, followed by Sephadex LH-20, 50% chloroform/hexane)

Sources & evidence

ORD record
ord-3b23c6d0e3b74aa8906dd3d34f096351
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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