Triphenylphosphine → Methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate

HRID 2423450Notes

Reaction equation

HRID 2423450 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[O:28][CH2:29][C:30]1[C:34]([CH2:35][OH:36])=[C:33]([CH:37]([CH3:39])[CH3:38])[O:32][N:31]=1.O[C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:56]=[C:55]3[C:50]([CH:51]=[C:52]([C:57]([O:59][CH3:60])=[O:58])[N:53]=[CH:54]3)=[CH:49][CH:48]=2)=[CH:43][CH:42]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[O:28][CH2:29][C:30]1[C:34]([CH2:35][O:36][C:41]2[CH:42]=[CH:43][C:44]([C:47]3[CH:56]=[C:55]4[C:50]([CH:51]=[C:52]([C:57]([O:59][CH3:60])=[O:58])[N:53]=[CH:54]4)=[CH:49][CH:48]=3)=[CH:45][CH:46]=2)=[C:33]([CH:37]([CH3:39])[CH3:38])[O:32][N:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59321463Methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylateHCID 59321512[3-{[(2,6-Dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol

Product 1

HCID 59321481Methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of triphenylphosphine (160 mg, 0.611 mmol), [3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (153 mg, 0.556 mmol) and methyl 7-(4-hydroxyphenyl)-3-isoquinolinecarboxylate (155 mg, 0.556 mmol) in dichloromethane (1.5 mL) was added diisopropyl azodicarboxylate (0.110 mL, 0.611 mmol) dropwise. The solution was heated in a microwave reactor at 90° C. for 10 minutes and then purified by chromatography (silica gel, 0-25% acetone in hexanes gradient elution) to afford methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate (109 mg, 37%). 1H-NMR (400 MHz, DMSO-d6) δ 9.11 (s, 1H), 8.64 (s, 1H), 8.50 (s, 1H), 8.29-8.20 (m, 2H), 7.86 (d, J=9 Hz, 2H), 7.19 (d, J=9 Hz, 2H), 7.00-6.90 (m, 3H), 5.09 (s, 2H), 4.90 (s, 2H), 3.91 (s, 3H), 3.41 (septet, J=7 Hz, 1H), 2.14 (s, 6H), 1.28 (d, J=7 Hz, 6H).

Workup

  1. custompurified by chromatography (silica gel, 0-25% acetone in hexanes gradient elution)

Sources & evidence

ORD record
ord-2f59ee3a7d2141a19ccc8176ff36e0af
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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