Simtuzumab → HCID 67974748, compound

HRID 1771463Notes

Reaction equation

[F:1][C:2]1[C:3](I)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[C:20]([Cl:27])[CH:19]=1)([OH:17])=[O:16]>>[Cl:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:3]1[C:2]([F:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[CH:4]=1)[C:15]([OH:17])=[O:16]

Participants

Reactant 2

HCID 17750227Simtuzumab

HCID 67974363HCID 67974363, compound2×

Product 1

HCID 67974748HCID 67974748, compoundYield 70%

Conditions

Temperature: 90 °C

Procedure

Followed the coupling procedure described in Step 1 of Example 20, where the starting materials were 3-fluoro-2-iodo-6-methoxynaphthalene (Intermediate 6) and 4-carboxy-2-chlorophenylboronic acid and wherein the reaction was heated to 90° C. for 3 hours. The desired product (380 mg, yield 70%) was isolated as a solid after workup.

Sources & evidence

ORD record: ord-3d821115e7704547ab6caa29324ba42d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249132B2

Reaction notes

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