Triethylamine → HCID 91382433, compound

HRID 2307772Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([Sn](C)(C)C)[CH:19]=2)=[CH:2]1.Br[C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42](=[O:43])[NH:41][C:39](=[O:40])[C:38]=12.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.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]>[O:40]=[C:39]1[C:38]2[C:37](=[CH:36][C:35]([C:18]3[CH:19]=[C:14]([O:13][CH2:12][C@@H:11]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:10][C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)[CH:15]=[N:16][CH:17]=3)=[CH:34][CH:33]=2)[C:42](=[O:43])[NH:41]1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of Example 32A (0.2 g, 0.31 mmol) and 6-bromophthalimide (0.084 g, 0.4 mmol) in DMF (2 mL) was treated with Pd2dba3 (0.04 g, 0.02 mmol), tri-o-tolylphosphine (0.02 g, 0.01 mmol), and triethylamine (0.06 mL, 0.4 mmol). The reaction was heated to 75° C. for 6 hours in a sealed tube and concentrated. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide the desired product (0.116 g, 55%).

Workup

concentrationconcentrated
customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-4124aa48197442a9a301d9f47918ca9d
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831175B2

Reaction notes

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