1-isopropyl-6-nitro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole → 1-Isopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-6-amine
Reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:5]1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[C:6]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:5]1)([CH3:3])[CH3:2]Participants
Procedure
Method P Add a solution of 1-isopropyl-6-nitro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, (4, R1=i-Pr) (14.48 g, 43.88 mmol) in ethanol to a suspension of 5% palladium on carbon (1.44 g) and ethanol in a Parr reaction bottle. Place the contents of the reaction bottle under a hydrogen atmosphere (60 psi) and shake on a Parr shaker at room temperature for 18 hr. After 18 hr, filter the contents of the reaction vessel through a pad of Celite, and concentrate the resulting filtrate in vacuo. The resulting crude, light-pink, crystalline material (11.84 g, 90%) can be used without further purification. 1H NMR (DSMO-d6) δ 7.39 (s, 1H), 7.39 (d, 1H, J=8.3 Hz), 6.54 (d, 1H, J=1.8 Hz), 6.41 (dd, 1H, J=8.3 Hz, 1.8 Hz), 4.73 (br s, 2H), 4.37 (septet, 1H, J=6.8 Hz), 1.37 (d, 6H, J=6.8 Hz), 1.23 (br s, 12H); MS (API ES+) m/e 301 (M+1).
Workup
- customin a Parr reaction bottle
- waitAfter 18 hr
- filtrationfilter the contents of the reaction vessel through a pad of Celite
- concentrationconcentrate the resulting filtrate in vacuo
- customThe resulting crude, light-pink, crystalline material (11.84 g, 90%) can be used without further purification
Sources & evidence
- ORD record
- ord-eccc037adeae4422a271415771603fd0
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932284B2
Reaction notes
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