Water → HCID 57585828, compound

HRID 70274Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]2.O.[CH3:20][N:21](C=O)C>[NH4+].[Cl-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:20]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]2)#[N:21]

Participants

Conditions

Temperature: 110 °C

Procedure

A flask charged with 1,1-dimethylethyl (5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate (3.0 g, 9.26 mmol; step 1 above), dppf (645 mg, 1.16 mmol), Pd2dba3 (532 mg, 0.58 mmol), ZnCN2 (1.50 g, 12.8 mmol) and water in 50 mL DMF was evacuated/backfilled with nitrogen (×4), and stirred at 110° C. for 21 hours. Upon cooling, the mixture was diluted with satd NH4Cl and extracted with ethyl acetate. The organic extract was washed with (water 3×, brine), dried over MgSO4 and concentrated in vacuo. The residual oil was purified by flash chromatography (ethyl acetate/hexanes) affording title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1 H), 7.45 (d, 1 H, J=7.9 Hz), 7.28 (d, 1 H, J=7.7 Hz), 4.69 (br.s, 1 H), 4.47 (br. s, 1 H), 3.33-3.25 (m, 2H), 2.86-2.80 (m, 2H), 2.79 (s, 9H).

Workup

temperatureUpon cooling
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with (water 3×, brine)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residual oil was purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-77bec987ac4b4b7fb84dd7c20ac2a17d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822518B2

Reaction notes

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