Dichloromethane → HCID 66795972, compound

HRID 1944811Notes

Reaction equation

HRID 1944811 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1.[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23].ClCCl.ClCCl.CO>C1COCC1>[C:22]([NH:26][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 21226129Dichloromethane methanolHCID 667958652-[2-(Bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 66795972HCID 66795972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 30.0 g (86.5 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 91.0 ml (63.3 g, 865 mmol) of tert-butylamine in 200 ml of THF was stirred at room temperature for 48 h. The resulting mixture was filtered through glass frit (G3) and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 urn; eluent: dichloromethane and then dichloromethane-methanol=1:1, vol.). Yield 27.4 g (94%). Anal. Calc. for C21H30BNO2: C, 74.34; H, 8.91; N, 4.13. Found: C, 74.49; H, 9.09; N, 3.98. 1H NMR (CDCl3): 8.80 (br. s, 1H, NH), 8.53 (m, 1H, 8-H in naphthyl), 7.88 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.83 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.71 (m, 1H, 5-H in naphthyl), 7.47 (m, 1H, 7-H in naphthyl), 7.41 (m, 1H, 6-H in naphthyl), 4.44 (s, 2H, CH2N), 1.49 (s, 12H, CMe2CMe2), 1.41 (s, 9H, tBu).

Workup

  1. filtrationThe resulting mixture was filtered through glass frit (G3)
  2. customevaporated to dryness
  3. customThe product was isolated by flash chromatography on silica gel 60 (40-63 urn

Sources & evidence

ORD record
ord-6e056ccc6f6b4abeb71cd42568689f4b
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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