2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 59375069, compound

HRID 1811151Notes

Reaction equation

HRID 1811151 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:8][C:9]=1[NH:10]2.[CH3:29][C:30]1[C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=[CH:33][C:31]=1[NH2:32]>>[NH2:32][C:31]1[C:30]([CH3:29])=[C:36]([C:2]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]3[C:3]=2[C:4]2[CH2:5][CH2:6][CH:7]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:8][C:9]=2[NH:10]3)[CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline2×HCID 66605632HCID 66605632, compound2×

Product 1

HCID 59375069HCID 59375069, compound

Procedure

Using the procedure of Example 3-2, benzyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate (Intermediate 50-4(a), 300 mg, 0.678 mmol) and 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (Intermediate 50-1, 237 mg, 1.017 mmol) were converted into benzyl 5-(3-amino-2-methylphenyl)-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, TFA salt, isolated as a white solid after preparative HPLC purification (60 mg, 15%). 1H NMR (400 MHz, methanol-d4) δ 7.63 (1 H, dd, J=7.7, 2.9 Hz), 7.18-7.46 (8 H, m), 6.82 (1H, dd, J=7.5, 2.8 Hz), 5.10 (2 H, s), 3.90 (1 H, br. s.), 3.14 (1 H, d, J=4.8 Hz), 2.72 (1H, br. s.), 1.77-2.19 (6 H, m), 1.51-1.68 (1 H, m). Mass spectrum m/z 469.3 (M+H)+.

Workup

  1. customisolated as a white solid
  2. customafter preparative HPLC purification (60 mg, 15%)

Sources & evidence

ORD record
ord-523a8fdfd66247a9968ea483dd690afe
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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