tert-Butanol → HCID 44465850, compound

HRID 241613Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:9]3[C:14]([C:15]=2C(O)=O)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[O:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49]C)CC)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:49](=[O:34])[NH:46][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[C:7]=1[C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH3:26])([CH3:54])([CH3:53])[CH3:52]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 44465847HCID 44465847, compound

Product 1

HCID 44465850HCID 44465850, compound

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indole-3-carboxylic acid (Example 8), diphenylphosphoryl azide (1.1 eq) and triethyl amine (1.1 eq) in tert-BuOH was heated in microwave reactor at 90° C. for 1 hour. After cooling, the mixture was subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, to provide [2-(3,5-dimethyl-isoxazol-4-yl)-1-(4-hydroxy-phenyl)-1H-indol-3-yl]-carbamic acid tert-butyl ester (E12). ES/MS m/z: 420.21 (M+H), 418.22 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.61 (m, 1H), 7.26-7.13 (m, 5H), 6.93 (m, 2H), 2.22 (s, 3H), 1.89 (s, 3H) and 1.44 (s, 9H).

Workup

temperatureAfter cooling
customevaporated

Sources & evidence

ORD record: ord-fd858d870d094be7ab5d36e0584f514f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653072B2

Reaction notes

Loading…