Triethylamine → HCID 59316974, compound

HRID 716750Notes

Reaction equation

HRID 716750 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:17])[N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]#[CH:20].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CN(C=O)C.[Cu]I>[CH2:11]([N:10]([CH2:14][CH2:15][CH3:16])[C:9](=[O:17])[NH:8][C:4]1[CH:3]=[C:2]([C:20]#[C:19][CH2:18][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH:7]=[CH:6][CH:5]=1)[CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 59316968HCID 59316968, compound

Product 1

HCID 59316974HCID 59316974, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-(3-bromophenyl)-1,1-dipropylurea (24) (0.507 g, 1.70 mmol), tert-butyl prop-2-ynylcarbamate (15) (0.323 g, 2.12 mmol), tri-o-tolylphosphine (0.0342 g, 0.112 mmol) and Et3N (3.0 mL) in DMF was degassed by bubbling argon for 10 min, and applying vacuum/argon 3×. PdCl2(Ph3P)2 (0.0434 g, 0.062 mmol) followed by CuI (0.0263 g, 0.138 mmol) were added and the mixture was degassed by applying vacuum/argon 3×. The reaction mixture was stirred under argon at 70° C. for 22 hrs. The reaction mixture was concentrated under reduced pressure. Purification by flash chromatography (10% to 50% EtOAc—hexanes gradient) gave tert-butyl 3-(3-(3,3-dipropylureido)phenyl)prop-2-ynylcarbamate (25) as a pale yellow solid. Yield (0.174 g, 28%); 1H NMR (400 MHz, DMSO-d6) δ 8.15 (br.s, 1H), 7.56 (t, J=1.8 Hz, 1H), 7.42-7.46 (m, 1H), 7.31 (br.t, 1H), 7.17 (t, J=7.8 Hz, 1H), 6.89-6.93 (m, 1H), 3.93 (d, J=5.7 Hz, 2H), 3.21 (t, J=7.6 Hz, 4H), 1.47 (sextet, J=7.4 Hz, 4H), 1.32-1.38 (m, 9H), 0.82 (t, J=7.4 Hz, 6H).

Workup

  1. customby bubbling argon for 10 min
  2. additionwere added
  3. customthe mixture was degassed
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customPurification by flash chromatography (10% to 50% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-c5b69682a5d84faba72e72c709a47af2
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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