Water → 2-Methyl-N-{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}aniline

HRID 634064Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[B:21]1[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[B:21]1[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 10.8 g (101 mmol) of 2-methylaniline, 23.3 g (67.0 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 10.2 g (74.0 mmol) of K2CO3 in 450 cm3 of DMF was stirred for 12 h at 80° C. The resulting mixture was poured into 1000 cm3 of water. The product was extracted with 3×200 ml of ethyl acetate. The combined extract was dried over MgSO4 and then evaporated to dryness. The residue was re-crystallized from a mixture of 200 ml of hexane and 10 ml of ethyl acetate. Yield 15.7 g (63%) of brown crystalline powder. Anal. calc. for C24H28BNO2: C, 77.22; H, 7.56; N, 3.75. Found: C, 77.33; H, 7.67; N, 3.59. 1H NMR (CDCl3): δ 8.20 (m, 1H, 8-H in naphthyl), 7.84 (d, J=8.5 Hz, 1H, 4-H in naphthyl), 7.82 (m, 1H, 5-H in naphthyl), 7.42-7.52 (m, 3H, 3, 6, 7-H in naphthyl), 7.14 (m, 1H, 5-H in 2-MeC6H4), 7.05 (m, 1H, 3-H in 2-MeC6H4), 6.78 (m, 1H, 6-H in 2-MeC6H4), 6.68 (m, 1H, 4-H in 2-MeC6H4), 4.53 (s, 2H, CH2NH), 3.95 (br.s, 1H, NH), 2.11 (s, 3H, Me), 1.36 (s, 12H, BPin).

Workup

extractionThe product was extracted with 3×200 ml of ethyl acetate
extractionThe combined extract
dry with materialwas dried over MgSO4
customevaporated to dryness
customThe residue was re-crystallized from a mixture of 200 ml of hexane and 10 ml of ethyl acetate

Sources & evidence

ORD record: ord-119cf81461e44a42b13e4525f1beb9c9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321858B2

Reaction notes

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