Triphenylphosphine → HCID 59300466, compound

HRID 2235944Notes

Reaction equation

HRID 2235944 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:12]([C:20]([F:23])([F:22])[F:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH2:24]([O:26][C:27](=[O:39])[CH2:28][C@H:29]1[C:37]2[C:32](=[CH:33][C:34](O)=[CH:35][CH:36]=2)[CH2:31][CH2:30]1)[CH3:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:34]3[CH:33]=[C:32]4[C:37](=[CH:36][CH:35]=3)[C@H:29]([CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:39])[CH2:30][CH2:31]4)[C:12]([C:20]([F:21])([F:23])[F:22])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 59444621HCID 59444621, compound

Product 1

HCID 59300466HCID 59300466, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl]amino}-1-propanol (Example 316) (0.34 g, 1.05 mmol) and ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 0.18 g, 0.84 mmol) in THF (8.50 mL) was added PPh3 (0.29 g, 1.09 mmol) and ADDP (0.28 g, 1.09 mmol) under argon. The golden yellow mixture was stirred at rt for 18 h, and then concentrated under reduced pressure. The product (0.33 g, 74%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 7.99 (d, 2H), 7.72 (d, 1H), 7.25 (d, 2H), 7.12 (d, 1H), 7.01 (d, 1H), 6.76 (d, 1H), 6.68 (dd, 1H), 4.15 (q, 2H), 4.08 (t, 2H), 3.82 (t, 2H), 3.45 (qt, 1H), 2.90-2.68 (m, 5H), 2.42-2.28 (m, 2H), 2.16 (qt, 2H), 1.78-1.68 (m, 1H), 1.30-1.24 (m, 6H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3fb273df3b447f4bfe1bdd4e601491a
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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