Trifluoroacetic acid → HCID 67237682, compound

HRID 1470968Notes

Reaction equation

C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=O)=[CH:11][CH:10]=1.[C:30]([C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].CCOCC.O>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:38]([C:37]3[CH:39]=[CH:40][C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:35][CH:36]=3)[C:18]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

TFA (0.6 mL, 7.79 mmol) was added to a mixture of the product from Example 39A (1.2335 g, 3.41 mmol) and 4-tert-butylaniline (0.8 mL, 5.07 mmol) in toluene (30 mL) and heated at 110° C. for 17 hours. The cooled reaction mixture was poured into ether/water and stirred until nice solid formed. The mixture was filtered to afford the title compound. 1H NMR (400 MHz, BENZENE-D6) δ 1.02 (s, 9H), 6.48 (d, J=3.8, 1H), 6.52 (d, J=3.8, 1H), 6.63 (d, J=8.5, 2H), 6.80 (d, J=8.5, 2H), 6.84 (d, J=8.9, 2H), 6.89 (d, J=8.5, 2H), 7.10 (d, J=8.5, 2H), 7.70 (d, J=8.9, 2H).

Workup

customThe cooled reaction mixture
customformed
filtrationThe mixture was filtered

Sources & evidence

ORD record: ord-60b2fbe5386f44aebb8a64edec363277
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006387B2

Reaction notes

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